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Direct organocatalytic asymmetric Mannich-type reactions in aqueous media: one-pot Mannich-allylation reactions

✍ Scribed by Armando Córdova; Carlos F Barbas III

Book ID
104252972
Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
101 KB
Volume
44
Category
Article
ISSN
0040-4039

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✦ Synopsis

The first direct organocatalytic asymmetric Mannich-type reactions in aqueous media are demonstrated herein. L-Proline-catalyzed reactions in aqueous media to provide b-formyl substituted a-amino acid derivatives with excellent diastereoselectivities (dr up to 19:1, syn/anti ) and high enantioselectivities (ee between 72 and >99%). These conditions provided for the development of novel one-pot asymmetric syntheses of cyclic g-allyl substituted a-amino acid derivatives (ee up to >99%). This was accomplished by combining the proline-catalyzed Mannich-type reactions with indium promoted allylations in aqueous media.

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✍ Takahiko Akiyama; Jun Takaya; Hirotaka Kagoshima 📂 Article 📅 2002 🏛 John Wiley and Sons 🌐 English ⚖ 126 KB 👁 1 views

HBF 4 -catalyzed Mannich-type reaction of silyl enolates with aldimines took place smoothly in aqueous organic solvent to afford b-aminocarbonyl compounds in high yields. The HBF 4 -catalyzed Mannich-type reaction also proceeded smoothly in water without organic solvent in the presence of a surfacta